Where should I go? Meet the destination checklist

Miles and Points obsessives play a fun game called “chase the fare”. If you’re not familiar, when some crazy low airfare or award ticket deal comes up, you don’t think, you just book…and then figure out what you will do when you get there. It’s why you’ll see bunches of folks on social media going to and from the same random places within a short period of time.

To the average traveler, it’s just a weird way to spend your precious two weeks vacation a year. I get that. You probably have your “top five” in mind. Let me guess: Paris, London, Rome, Hawaii, Australia. Am I close? Twenty five years of close to full time travel and you pretty much figure out what people dream of.

Now let me ask you a question: Why (Paris, London, Rome, Hawaii, Australia)? Can you really give an answer that doesn’t come out of a rom-com? Here’s where I ask you to take a page from the fare chasers. I don’t want you to go quite as far down the road to the loony bin as many of the travel nerds I’ve met (and I say that as a fellow nerd) but one thing they’ve got right is flexibility.

When you think about your next trip, I want you to think about the experience you want first, then choose a destination.

The destination checklist

Over the years I’ve become pretty good at narrowing down where I want to go. When I start to plan a trip, the first thing I do is complete the destination checklist because I know choosing a place that fits is the single most important determination as to whether or not I’ll enjoy a trip.

Do I want an active trip or a restful one?
Urban, Rural, or a mix?
One destination or moving around?
Luxury or simplicity?
Developed or developing region?
Am I limited by the calendar?
By the climate or the seasons?
What is my cash budget?
What is miles/points budget?
Are there any sweet spots in my miles/points programs that fit the above criteria?
What about other promotions?

How this works

Last year I had the week before Easter free for a week-long solo trip. I knew I wanted to swim in the ocean, but didn’t necessarily want a beach resort with nothing else to do.

Using my checklist, I narrowed down my options as such:

Do I want an active trip or a restful one? mix
Urban, Rural, or a mix? mix
One destination or moving around? Moving around, but within a limited area and no more than one move.
Luxury or simplicity? Flex
Developed or developing? Flex, but not remote.
Am I limited by the calendar? Very! Must be spring break and only a week. Takes out Asia and Southern South America.
By the climate or the seasons? Yes. Dates make much of North America and Europe too cold.

This was a good point for at least a partial decision…Mexico or Central America it is!

What is my cash budget? Like to be under 1K
What is miles/points budget? Like to keep it under 100K points total ($1,000 value)
Are there any sweet spots in my miles/points programs that fit the above criteria? Copa flies from many US gateways and award tickets are easy to find.
What about other promotions? $200 Delta Stays credit to use up

Winner Winner chicken dinner! Panama it was. I spent five nights in the city using Choice points and my Delta Stays credit at the Gamboa Rainforest Resort. I got to swim in the ocean, but also explored the jungle, strolled the Casco Antiguo and ate my weight in fresh fish.

The trip was exactly what I needed, so much so that I repeated it for my 2025 Spring Break. I enjoyed the Gamboa Rainforest Resort so much that I booked clients there for an upcoming trip.

I’ve returned to this checklist over and over again and it’s never steered me wrong. By thinking about the experience rather than the destination, my family has visited Oaxaca, Mexico, Beziers, France, Antigua, Guatemala, Sardinia, Gran Canaria and many other spots that aren’t at the tip of your tongue. Most recently it directed me to Montreal this summer when my daughter and I wanted a European vibe but didn’t have the time or budget to get to Europe.

How do you decide where to go? I’d love to hear your experiences in the comments.